m-Chloroperbenzoic acid → 5-Acetyl-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 1647151Notes

Reaction equation

HRID 1647151 reaction equation
[C:1]([C:4]1[C:24]([CH3:25])=[CH:23][C:7]2[NH:8][C:9]([S:11][CH2:12][C:13]3[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[CH:16]=[CH:15][N:14]=3)=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].C([O-])(O)=[O:27].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl.O>[C:1]([C:4]1[C:24]([CH3:25])=[CH:23][C:7]2[NH:8][C:9]([S:11]([CH2:12][C:13]3[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[CH:16]=[CH:15][N:14]=3)=[O:27])=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 199264555-Acetyl-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

Product 1

HCID 199264745-Acetyl-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

5-Acetyl-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole (3.75 g, 10 mmol) was dissolved in CH2Cl2 (70 ml). NaHCO3 (1.76 g, 21 mmol) in H2O (25 ml) was added and the mixture was cooled to ≈+3° C. m-Chloroperbenzoic acid 69.5% (2.43 g, 9.8 mmol) dissolved in CH2Cl2 (20 ml) was added dropwise under stirring. Stirring was continued for 10 min. The phases were separated and the organic phase was dried over Na2SO4 and evaporated under reduced pressure. The residue was crystallized from CH3CN giving the title compound (2.25 g, 60%).

Workup

  1. additionwas added dropwise
  2. stirringStirring
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was crystallized from CH3CN giving the title compound (2.25 g, 60%)

Sources & evidence

ORD record
ord-e0dfe599d14e4078ad23f3028e8bf7db
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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